Darrell Winfield, better known as the Marlboro Man died Monday at the age of 85. Winfield was the face of the cigarette conglomerate from the 1960’s until the 1980’s. The company opted for actual cowboys rather than actors in their famous advertising campaign.

One of the last remaining Marlboro Men rode off into the sunset this week. Darrell Hugh Winfield died Monday in his Riverton, Wyo., home, The Associated Press reported. His craggy, handsome face epitomized the macho cowboy image used to market Marlboro Reds until the 1990s — mostly to men, although the ads obviously had a certain appeal for women, too. The Oklahoma native was one of the last Marlboro Men alive. At least four of them died from smoking-related illnesses, according to a 2014 report